WO2021206502A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2021206502A1
WO2021206502A1 PCT/KR2021/004481 KR2021004481W WO2021206502A1 WO 2021206502 A1 WO2021206502 A1 WO 2021206502A1 KR 2021004481 W KR2021004481 W KR 2021004481W WO 2021206502 A1 WO2021206502 A1 WO 2021206502A1
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김민준
이동훈
서상덕
오중석
이다정
최승원
심재훈
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주식회사 엘지화학
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Priority claimed from KR1020210046082A external-priority patent/KR102576736B1/ko
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Priority to CN202180004507.2A priority Critical patent/CN114144902A/zh
Publication of WO2021206502A1 publication Critical patent/WO2021206502A1/fr

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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic light emitting device.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
  • An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • a voltage when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to an organic light emitting device having improved driving voltage, efficiency, and lifetime.
  • the present invention provides the following organic light emitting device:
  • anode anode
  • cathode anode
  • a light emitting layer between the anode and the cathode
  • the light emitting layer comprises a compound represented by the following formula (1) and a compound represented by the following formula (2),
  • L 1 is a single bond; Or a substituted or unsubstituted C 6-60 arylene,
  • L 2 and L 3 are each independently a single bond; Or a substituted or unsubstituted C 6-60 arylene,
  • Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 5-60 heteroaryl comprising any one or more selected from the group consisting of N, O and S,
  • R is hydrogen, deuterium, or substituted or unsubstituted C 6-60 aryl
  • L 4 is a single bond; Or a substituted or unsubstituted C 6-60 arylene,
  • L 5 and L 6 are each independently a single bond; Or a substituted or unsubstituted C 6-60 arylene,
  • Ar 3 and Ar 4 are each independently substituted or unsubstituted C 6-60 aryl; or C 5-60 heteroaryl including at least one selected from the group consisting of substituted or unsubstituted N, O and S.
  • the organic light emitting device described above has excellent driving voltage, efficiency, and lifetime.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 .
  • FIG. 2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), an electron transport layer (7), an electron injection layer (8) and a cathode (4) It shows an example of the organic light emitting device made up.
  • substituted or unsubstituted refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • the number of carbon atoms in the carbonyl group is not particularly limited, but preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms.
  • a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted, etc. can be
  • the present invention is not limited thereto.
  • the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothioph
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group.
  • heteroaryl among heteroarylamines the description of the above-described heterocyclic group may be applied.
  • the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group.
  • the description of the above-described aryl group may be applied except that arylene is a divalent group.
  • the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents.
  • the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.
  • the anode and cathode used in the present invention mean electrodes used in an organic light emitting device.
  • anode material a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer.
  • the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the light emitting layer used in the present invention refers to a layer capable of emitting light in the visible ray region by combining holes and electrons transferred from the anode and the cathode.
  • the emission layer includes a host material and a dopant material, and in the present invention, the compound represented by Formula 1 and the compound represented by Formula 2 are included as hosts.
  • Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-4.
  • L 1 to L 3 , Ar 1 , Ar 2 and R are as defined above.
  • L 1 is a single bond, phenylene, or naphthylene. More preferably, L 1 is a single bond, , or am.
  • L 2 and L 3 are each independently a single bond, phenylene, or naphthylene.
  • Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, naphthylphenyl, phenylnaphthyl, dimethylfluorenyl, dibenzofu ranyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl;
  • the Ar 1 and Ar 2 are each independently unsubstituted or substituted with one or more deuterium.
  • R is hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl.
  • the present invention provides a method for preparing a compound represented by Formula 1 as shown in Scheme 1 below.
  • Each of the above reactions is a Suzuki coupling reaction, and preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art.
  • the manufacturing method may be more specific in Preparation Examples to be described later.
  • L 4 is a single bond or phenylene.
  • L 5 and L 6 are each independently a single bond, or phenylene.
  • Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, sp It is robifluorenyl.
  • the reaction is an amine substitution reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art.
  • the manufacturing method may be more specific in Preparation Examples to be described later.
  • the weight ratio of the compound represented by Formula 1 to the compound represented by Formula 2 is 1:99 to 99:1, 5:95 to 95:5, or 10:90 to 90:10.
  • the dopant material is not particularly limited as long as it is a material used in an organic light emitting device.
  • Examples include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group
  • the styrylamine compound is a substituted or unsubstituted derivative.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the organic light emitting diode according to the present invention may include a hole transport layer between the electron blocking layer and the anode.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer.
  • the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the organic light emitting diode according to the present invention may further include a hole injection layer between the anode and the hole transport layer, if necessary.
  • the hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect with respect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • a compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.
  • the organic light emitting device may include an electron transport layer between the light emitting layer and the cathode.
  • the electron transport layer is a layer that receives electrons from the electron injection layer formed on the cathode or the cathode, transports electrons to the light emitting layer, and suppresses the transfer of holes in the light emitting layer.
  • an electron transport material electrons are well injected from the cathode
  • a material that can receive and transfer to the light emitting layer a material with high electron mobility is suitable.
  • the electron transport material include an Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer may be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.
  • the organic light emitting diode according to the present invention may further include an electron injection layer between the electron transport layer and the cathode, if necessary.
  • the electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. It is preferable to use a compound which prevents movement to a layer and is excellent in the ability to form a thin film.
  • the material that can be used as the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preole nylidene methane, anthrone, and the like, derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • the metal complex compound examples include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc.
  • the present invention is not limited thereto.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 .
  • FIG. 2 shows the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, the electron transport layer 7, the electron injection layer 8 and the cathode 4 ) shows an example of an organic light emitting device made of
  • the organic light emitting device may be manufactured by sequentially stacking the above-described components. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. And, after forming each of the above-mentioned layers thereon, it can be prepared by depositing a material that can be used as a cathode thereon.
  • PVD physical vapor deposition
  • an organic light emitting device may be manufactured by sequentially depositing the anode material on the substrate in the reverse order of the above-described configuration from the cathode material (WO 2003/012890).
  • the light emitting layer may be formed by a solution coating method as well as a vacuum deposition method for the host and dopant.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • the organic light emitting device may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 ⁇ , but the A-1 compound was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 ⁇ .
  • the following EB-1 compound was vacuum-deposited to a thickness of 150 ⁇ on the hole transport layer to form an electron blocking layer.
  • the previously prepared compound 1-2, compound 2-1 (above, host) and the following Dp-7 compound (red dopant) were vacuum co-deposited at a weight ratio of 49:49:2.
  • a red light emitting layer having a thickness of 400 ⁇ was formed.
  • a hole blocking layer was formed by vacuum-depositing the following HB-1 compound to a thickness of 30 ⁇ on the light emitting layer. Then, the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole blocking layer at a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • the deposition rate of organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 ⁇ /sec
  • the deposition rate of aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 2 ⁇ 10 -
  • an organic light emitting device was manufactured.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Tables 1 to 4 were used instead of Compound 1-2 and Compound 2-1, respectively.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Tables 5 to 8 were used instead of Compound 1-2 and Compound 2-1, respectively.
  • the compounds shown in Tables 5 to 8 are as follows.
  • the combination of the compound of Formula 1, which is the first host, and the compound of Formula 2, which is the second host, of the present invention transfers energy to the red dopant in the red light emitting layer well, and thus the voltage is improved, and the efficiency and lifespan are improved. rise can be seen. It is confirmed that the combination of the compound of Formula 1 and the compound of Formula 2 of the present invention, rather than the combination with the compound of Comparative Example, increases the efficiency and lifespan by combining electrons and holes through a more stable balance in the light emitting layer to form excitons. could Therefore, it can be confirmed that the driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting device can be improved when the compound of Formula 1 and the compound of Formula 2 are combined and used as a host for the red light emitting layer by co-evaporation.
  • Substrate 2 Anode

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique l'utilisant.
PCT/KR2021/004481 2020-04-09 2021-04-09 Élément électroluminescent organique WO2021206502A1 (fr)

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KR20150007139A (ko) * 2013-07-10 2015-01-20 제일모직주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
KR20170049440A (ko) * 2015-10-27 2017-05-10 주식회사 엘지화학 유기 발광 소자
KR101847347B1 (ko) * 2017-06-30 2018-04-09 주식회사 두산 유기 화합물 및 이를 이용한 유기 전계 발광 소자
WO2019031605A1 (fr) * 2017-08-10 2019-02-14 東ソー株式会社 Composé cyclique fusionné
WO2019066250A1 (fr) * 2017-09-29 2019-04-04 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique comprenant celui-ci

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JP5844384B2 (ja) * 2010-12-29 2016-01-13 エルジー・ケム・リミテッド 新規な化合物およびこれを用いた有機発光素子
KR102064992B1 (ko) * 2017-05-22 2020-01-10 주식회사 엘지화학 신규한 헤테로고리 화합물 및 이를 이용한 유기발광 소자
KR102142676B1 (ko) * 2017-10-24 2020-08-07 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR102202593B1 (ko) * 2018-05-28 2021-01-13 주식회사 엘지화학 신규한 트리페닐렌 화합물 및 이를 이용한 유기 발광 소자

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150007139A (ko) * 2013-07-10 2015-01-20 제일모직주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
KR20170049440A (ko) * 2015-10-27 2017-05-10 주식회사 엘지화학 유기 발광 소자
KR101847347B1 (ko) * 2017-06-30 2018-04-09 주식회사 두산 유기 화합물 및 이를 이용한 유기 전계 발광 소자
WO2019031605A1 (fr) * 2017-08-10 2019-02-14 東ソー株式会社 Composé cyclique fusionné
WO2019066250A1 (fr) * 2017-09-29 2019-04-04 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique comprenant celui-ci

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